The Badia Fiorentina is home to one of Filippino Lippi's most beautiful paintings, the Apparition of the Virgin to St Bernard (c. 1485).

The painting was originally commissioned by Piero di Francesco del Pugliese (who appears, hands clasped in prayer, in the bottom right corner) for the small monastery of Santa Maria alle Campora di Marignolle, which lay outside the Porta Romana. The monastery was controlled by the Badia Fiorentina and during the 1529 siege of Florence, when the troops of emperor Charles V occupied the entire southern perimeter of the city, the monks moved the painting to their church inside the city walls.

The Virgin Mary appears to St Bernard, who is writing at a makeshift desk. A chained demon crouches in the rocks behind the saint. The demon, who is trying to break free of his chains, is a reference to a medieval hymn celebrating the Virgin as the liberator of humanity from the chains of their sins.